Water → 1-(2,2-Diethoxyethyl)-2-trichloroacetylpyrrole

HRID 2248591Notes

Reaction equation

HRID 2248591 reaction equation
[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)[CH3:2].N1C(C)=CC=CC=1C.[Cl:22][C:23]([Cl:28])([Cl:27])[C:24](Cl)=[O:25].O>C(Cl)(Cl)Cl>[CH2:12]([O:11][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:24](=[O:25])[C:23]([Cl:28])([Cl:27])[Cl:22])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6420Trichloroacetyl chlorideHCID 79372,6-LutidineHCID 19994527HCID 19994527, compound

Product 1

HCID 156620861-(2,2-Diethoxyethyl)-2-trichloroacetylpyrroleYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a refluxing solution of 1-(2,2-diethoxyethyl)pyrrole (31.6 g, 172.5 mmol) and 2,6-lutidine (20.3 g, 189.8 mmol) in 90 mL of chloroform over a period of 16 hours was added trichloroacetyl chloride (34.5 g, 189.8 mmol) in 90 mL of chloroform. The reaction mixture was refluxed for an additional 4 hours. The reaction mixture was allowed to cool to room temperature and then poured into a mixture of water and chloroform (1:1). The phases were separated, washed with a saturated solution of NaCl, dried over MgSO4, and then evaporated. Purification of the product by column chromatography [hexane:ether (9.9:0.1)] gave the title compound, 1-(2,2-diethoxyethyl)-2-trichloroacetylpyrrole, in 60% yield, ms 327 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for an additional 4 hours
  2. customThe phases were separated
  3. washwashed with a saturated solution of NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customPurification of the product by column chromatography [hexane:ether (9.9:0.1)]

Sources & evidence

ORD record
ord-5ed0a268fc864bb0b0f1e1d19155e6dd
Source dataset
uspto-grants-1991_08
Patent number
US05041442

Reaction notes

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